2-(p-Nitrophenyl)-4H-1,3-benzoxazin-4-one | 25225-69-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并恶嗪类
• 英文名称: 2-(p-Nitrophenyl)-4H-1,3-benzoxazin-4-one
• 英文别名: 2-(4-nitro-phenyl)-benzo[e][1,3]oxazin-4-one；2-(4-nitrophenyl)-4H-1,3-benzoxazin-4-one；2-(4'-Nitrophenyl)-4H-1,3-benzoxazin-4-on；2-(4'-Nitrophenyl)-4H-1,3benzoxazin-4-on；2-(4-nitrophenyl)-1,3-benzoxazin-4-one
• CAS: 25225-69-8
• 化学式: C₁₄H₈N₂O₄
• 分子量: 268.229
• InChiKey: XGWIUACZLJQOPV-UHFFFAOYSA-N

物化性质

• 熔点：
  70-72 °C(Solv: dichloromethane (75-09-2))
• 沸点：
  462.1±47.0 °C(Predicted)
• 密度：
  1.43±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  20
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  84.5
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-肼基苯磺酰胺 、 2-(p-Nitrophenyl)-4H-1,3-benzoxazin-4-one 在 三乙胺 作用下， 以 乙醇 为溶剂， 以57.8 %的产率得到4-(5-(2-hydroxyphenyl)-3-(4-nitrophenyl)-1H-1,2,4-triazol-1-yl)benzenesulfonamide
  参考文献：
  名称：

  Synthesis of 1,3,5-triphenyl-1,2,4-triazole derivatives and their neuroprotection by anti-oxidative stress and anti-inflammation and protecting BBB

  摘要：

  DOI：

  10.1016/j.ejmech.2023.115742
• 作为产物：
  描述：

  水杨酰胺 在 sodium hydroxide 作用下， 以 水 、 乙二醇 为溶剂， 反应 4.5h， 生成 2-(p-Nitrophenyl)-4H-1,3-benzoxazin-4-one
  参考文献：
  名称：

  Lakhan, Ram; Singh, R. L., Journal fur praktische Chemie (Leipzig 1954), 1988, vol. 330, # 2, p. 299 - 304

  摘要：

  DOI：

文献信息

• Die Synthese von asymmetrisch substituierten o-Hydroxyphenyl-<i>s</i>-triazinen
  作者：H. Brunetti、C. E. Lüthi

  DOI：10.1002/hlca.19720550520

  日期：1972.7.10

  Mono- and bis-(2-hydroxyphenyl)-s-triazines 4, 14, 18, 22, 28, 29 can be prepared by (a) reaction of salicylic acid esters 2 with amidines 3; (b) reaction of 4H-1, 3-benzoxazin-4-ones 10 with amidines 3; and (c) Friedel-Crafts-reaction of chloro-s-triazines 26, 27 with resorcinol 24.

  单-和双- （2-羟基苯基） -小号-triazines 4，14，18，22，28，29可以通过水杨酸酯（a）的反应来制备2与脒3 ; （b）4 H -1，3-苯并恶嗪-4-酮10与am 3的反应；和（c）的Friedel-Crafts氯的-反应小号-triazines 26，27用间苯二酚24。
• Chemoselective Reaction of Benzoylisothiocyanates with Hydroxyl Group of Salicylamide: a New and Convenient Entry Into 2-Aryl-4<i>H</i>-benzo[e][1,3]oxazin-4-ones
  作者：Tarjeet Singh、Girija S. Singh、Ram Lakhan

  DOI：10.1080/10426507.2012.755974

  日期：2013.10.1

  Abstract The reactions of benzoylisothiocyanates with salicylamide in pyridine-xylene solution occurs chemoselectively at the hydroxyl group of the salicylamide to afford the corresponding O-benzoyl derivatives. The latter products, on prolonged heating in pyridine-xylene solution, undergo cyclodehydration to give 2-aryl-4H-benzo[e][1,3]oxazin-4-ones in good yields. These compounds could also be synthesized

  摘要 在吡啶-二甲苯溶液中，苯甲酰异硫氰酸酯与水杨酰胺在水杨酰胺的羟基上发生化学选择性反应，得到相应的O-苯甲酰衍生物。后一种产物在吡啶-二甲苯溶液中长时间加热后，会发生环脱水反应，以良好的收率得到 2-芳基-4H-苯并[e][1,3]恶嗪-4-酮。这些化合物也可以通过苯甲酰异硫氰酸酯与水杨酰胺的直接一锅反应合成，方法是在回流下将苯甲酰异硫氰酸酯缓慢加入水杨酰胺在二甲苯-吡啶溶液中的溶液中。产品已在令人满意的分析和光谱数据的基础上进行了表征。图形概要
• Substituted ureido-s-triazines
  申请人：Hoechst Aktiengesellschaft

  公开号：US03957780A1

  公开（公告）日：1976-05-18

  Hydroxyphenyl-ureido-s-triazines are prepared by reacting 4H-1,3-benzoxazin-4-ones with guanyl urea. The triazine derivatives are useful as UV stabilizers for plastic materials.

  羟基苯基脲基-s-三嗪是通过将4H-1,3-苯并噁嗪-4-酮与鸟氨酰脲反应制备而成。这种三嗪衍生物可用作塑料材料的紫外线稳定剂。
• Process for the production of benzoxazinones
  申请人：Ciba Specialty Chemicals Corporation

  公开号：US06040443A1

  公开（公告）日：2000-03-21

  There is described a process for the production of a 1,3-benzoxazin-4-one having the formula: ##STR1## in which R.sub.1 and R.sub.2, independently, are hydrogen, cyano, halogen, nitro, C.sub.1 -C.sub.20 alkyl, O--C.sub.1 -C.sub.20 alkyl, phenyl, NH--CO--C.sub.1 -C.sub.20 alkyl, N(R.sub.3).sub.2, SO.sub.2 N(R.sub.3).sub.2, COOR.sub.3 or CON(R.sub.3).sub.2 in which R.sub.3 is hydrogen, cyano, halogen, nitro, C.sub.1 -C.sub.20 alkyl, O--C.sub.1 -C.sub.20 alkyl, phenyl or NH--CO--C.sub.1 -C.sub.20 alkyl, comprising reacting, at elevated temperature, 1 molar equivalent of an o-hydroxybenzamide of formula: ##STR2## in which R.sub.1 has its previous significance, with 2 to 6 molar equivalents of a benzoyl chloride of formula: ##STR3## in which R.sub.2 has its previous significance. The 1,3-benzoxazin-4-ones having the formula (1) so obtained are important intermediates for the production of triazine compounds having excellent absorption spectrum characteristics and good resistance to exposure to UV light.

  描述了一种制备具有以下结构式的1,3-苯并噁嗪-4-酮的过程：##STR1## 其中R.sub.1和R.sub.2独立地为氢、氰、卤素、硝基、C.sub.1-C.sub.20烷基、O-C.sub.1-C.sub.20烷基、苯基、NH-CO-C.sub.1-C.sub.20烷基、N（R.sub.3）.sub.2、SO.sub.2N（R.sub.3）.sub.2、COOR.sub.3或CON（R.sub.3）.sub.2，其中R.sub.3为氢、氰、卤素、硝基、C.sub.1-C.sub.20烷基、O-C.sub.1-C.sub.20烷基、苯基或NH-CO-C.sub.1-C.sub.20烷基，包括在高温下反应式中1摩尔当量的具有以下结构式的o-羟基苯甲酰胺：##STR2## 其中R.sub.1具有其先前的意义，以及2至6摩尔当量的具有以下结构式的苯甲酰氯：##STR3## 其中R.sub.2具有其先前的意义。因此获得的具有结构式（1）的1,3-苯并噁嗪-4-酮是制备具有优异吸收光谱特性和良好耐紫外线曝露性的三嗪化合物的重要中间体。
• Synthesis and biological evaluation of 1,2,4-triazole derivatives as potential neuroprotectant against ischemic brain injury
  作者：Liping Liao、Caibao Jiang、Jianwen Chen、Jinguo Shi、Xinhua Li、Yang Wang、Jin Wen、Shujia Zhou、Jie Liang、Yaoqiang Lao、Jingxia Zhang

  DOI：10.1016/j.ejmech.2020.112114

  日期：2020.3

  A series of 1,2,4-triazole derivatives 1-14 was synthesized to investigate their neuroprotective effects and mechanisms of action. Compounds 5-11 noticeably protected PC12 cells from the cytotoxicity of H2O2 or sodium nitroprusside (SNP). Compound 11 was the most effective derivative. Compound 11 chelated Fe (II) iron, scavenged reactive oxygen species (ROS), and restored the mitochondrial membrane potential (MMP). Moreover, it enhanced the activity of the antioxidant defense system by increasing the serum level of superoxide dismutase (SOD) and promoting the nuclear translocation of nuclear factor erythroid 2-related factor 2 (Nrf2). Compound 11 caused certain improvements in behavior, the cerebral infarction area, and serum levels of biochemical indicators (TNF-alpha, IL-10, SOD and MDA) in a rat MCAO model. The lethal dose (LD50) of compound 11 in mice receiving intraperitoneal injections was greater than 400 mg/kg. Meanwhile, pharmacokinetic experiments revealed high bioavailability of this compound after both oral and intravenous administration (F = 60.76%, CL = 0.014 mg/kg/h) and a longer half-life (4.26 and 5.11 h after oral and intravenous administration, respectively). Based on these findings, compound 11 may be a promising neuroprotectant for the treatment of ischemic stroke. (C) 2020 Elsevier Masson SAS. All rights reserved.